Chicamycin A
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| Category | Antibiotics |
| Catalog number | BBF-00296 |
| CAS | 89675-37-6 |
| Molecular Weight | 294.30 |
| Molecular Formula | C14H18N2O5 |
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Description
Chicamycin A is produced by the strain of Streptomyces albus J576-99. It has anti-tumor activity and weak anti-gram-positive bacteria activity.
Specification
| Synonyms | 5H-Pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 1,2,3,10,11,11a-hexahydro-2,8-dihydroxy-7,11-dimethoxy-, (2S-(2-alpha,11-alpha,11b-beta))-; BRN 5763463 |
| IUPAC Name | (6R,6aS,8S)-3,8-dihydroxy-2,6-dimethoxy-5,6,6a,7,8,9-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one |
| Canonical SMILES | COC1C2CC(CN2C(=O)C3=CC(=C(C=C3N1)O)OC)O |
| InChI | InChI=1S/C14H18N2O5/c1-20-12-4-8-9(5-11(12)18)15-13(21-2)10-3-7(17)6-16(10)14(8)19/h4-5,7,10,13,15,17-18H,3,6H2,1-2H3/t7-,10-,13+/m0/s1 |
| InChI Key | FDZKMDGYTVIWIB-LCWDIZFYSA-N |
Properties
| Appearance | Colorless Acicular Crystalline |
| Antibiotic Activity Spectrum | gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | 161-163 °C |
Reference Reading
1. Chicamycin, a new antitumor antibiotic. II. Structure determination of chicamycins A and B
M Konishi, H Ohkuma, N Naruse, H Kawaguchi J Antibiot (Tokyo). 1984 Mar;37(3):200-6. doi: 10.7164/antibiotics.37.200.
Structures of chicamycins A and B have been determined from a series of chemical degradation studies coupled with spectroscopic analysis. Chicamycin A is 2(S),11(R), 11a (S)-1,2,3,10, 11, 11a -hexahydro-2,8-dihydroxy-7,11-dimethoxy-5H-pyrrolo-[2,1-c] [1,4]-benzodiazepin-5-one, and chicamycin B is 2(S), 11a (S)-1,2,3, 11a -tetrahydro-2,8-dihydroxy-7 -methoxy-5H-pyrrolo-[2,1-c][1,4]-benzodiazepin-5-one which is the demethanol form of chicamycin A. The structure of chicamycin B is closely related to that of neothramycin , differing only in the position of a hydroxyl substituent on the pyrrolidine ring.
2. Chicamycin, a new antitumor antibiotic. I. Production, isolation and properties
M Konishi, M Hatori, K Tomita, M Sugawara, C Ikeda, Y Nishiyama, H Imanishi, T Miyaki, H Kawaguchi J Antibiot (Tokyo). 1984 Mar;37(3):191-9. doi: 10.7164/antibiotics.37.191.
Chicamycin is a new antitumor antibiotic produced by a strain of Streptomyces albus, No. J576 -99. The antibiotic is extractable into organic solvents from the fermentation broth and is obtained in two active forms, chicamycins A and B, depending upon the isolation procedure used. Chicamycin A is not a natural antibiotic but the methanol adduct of naturally produced chicamycin B. Both forms of the antibiotic have weak antibacterial activity against some Gram-positive and acid-fast bacteria. They inhibit the growth of experimental tumors such as P388 mouse leukemia.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
